Hydrochloric Acid → HCID 20380005, compound

HRID 1448493Notes

Reaction equation

HRID 1448493 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:33])[CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19](O)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Cl>C(O)(C)C>[ClH:1].[C:26]1([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH2:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=3)=[O:33])[CH2:18][CH2:17]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2061821-Butanone, 1-(4-fluorophenyl)-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-, hydrochloride

Product 1

HCID 20380005HCID 20380005, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 17.7 g (0.038 mole) of 4'-fluoro-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone hydrochloride, 200 ml of 37% HCl, and 200 ml of isopropyl alcohol was heated on a steam bath for 4 hours. The solvent and excess acid were removed at reduced pressure. The remaining residue was treated with benzene and ethanol and heated to remove excess acid. The excess benzene and ethanol were removed, and the residue was dissolved in hot butanone to which ether was added. Upon cooling a solid formed which was recrystallized from ethyl acetate to give the desired product M.P. 190°-191° C.

Workup

  1. temperaturewas heated on a steam bath for 4 hours
  2. customThe solvent and excess acid were removed at reduced pressure
  3. additionThe remaining residue was treated with benzene and ethanol
  4. temperatureheated
  5. customto remove excess acid
  6. customThe excess benzene and ethanol were removed
  7. dissolutionthe residue was dissolved in hot butanone to which ether
  8. additionwas added
  9. temperatureUpon cooling a solid
  10. customformed which
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ab0f4d03dac6405881d937e0c05b6846
Source dataset
uspto-grants-1979_12
Patent number
US04180583

Reaction notes

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